In Anton Chekhov’s “The Seagull,” melancholy and despair are draped over with the elegance of Russian realism and restraint. Sure, his characters make terrible choices in life and love. But the deeper yearnings and fears that propel them to their unhappy endings remain grandly enigmatic.

For her contemporary adaptation of the 123-year-old classic at Serenbe Playhouse, director Elizabeth Dinkova showcases the dark primal impulse of Chekhov’s coterie of literary types and their courtesans as a masked vaudeville. Drawing on Greek tragedy, Sigmund Freud, Kurt Weill, Bertolt Brecht, and the swampy visual vocabulary of a TV horror series, Dinkova’s reimagining requires actors to break from the narrative to perform little song-and-dance numbers that afford a glimpse of their characters’ personal purgatory.

As usual for this Chattahoochee Hills theater known for its site-specific productions, the action transpires in an inspired natural setting. What a lovely touch that theatrical diva Irina (the terrific Park Krausen) and her circle of intimates retire to a country estate situated around an actual lake.

But there’s more: While smartly trimming the list of players to a manageable seven, Dinkova takes the bold move of changing the sex of one of them.

Irina’s son Constantine, a symbolist playwright struggling to create new forms for the theater, is now Constance (Maythinee Washington). In the story’s roundelay of unrequited love and heartbreak, Medvedenko (here called Simon and played by Skye Passmore) yearns for Masha (Brooke Owens), who in turn longs for Constance, who is actually smitten with the actress Nina (Shannon McCarren), who is crazy for Irina’s lover, Boris (Lee Osorio).

But in the case of Serenbe’s “The Seagull,” the switcheroo doesn’t quite work — for me, at least. Chekhov’s delicately calibrated machinations, on love and the politics of class and gender, lose their balance. Inserting a sinister, “Seven Deadly Sins”-style cabaret into the narrative is taxing enough on audience members. Reassigning Constantine’s sex asks even more. It comes across as rather self-indulgent and heavy-handed. Some of the mother-child tension, a la Oedipus and Jocasta and Hamlet and Gertrude, is lost.

That said, the ensemble, which also includes Allan Edwards as Irina’s long-ailing brother, Peter, is not to blame for the dramaturgical clumsiness. They are all quite good. In particular: Krausen is deliciously over-the-top as an insensitive and imperious mother. Washington is mesmerizing, if miscast, as her turbulent writer-daughter. And Osorio and Passmore give understated performances that feel true to the Chekhovian original.

As is often the case at Serenbe Playhouse, the visual artistry is stellar, too. (Scenic design is by Joel Coady and Barrett Doyle; costumes by An-Lin Dauber; lighting by Maranda DeBusk; and sound by Rob Brooksher.)

In the vaudeville interludes, Bubba Carr’s lurid dances allow the personalities to reveal their inner id, in ways that are by turns insightful and comic. But Anais Azul’s original, Balkan-inspired music can be raucous and jarring. In the end, “The Seagull,” which features a blood orgy of a finale, comes across as overly serious and overwrought. To say that it’s pretentious is putting it gently.

On a Facebook post, the theater states: “If you think Chekhov puts you to sleep, you won’t nap during our production of ‘The Seagull!’ “

Irina herself might beg to differ.

After drinking in the misery and stagnation that engulf the gathering at her brother’s lakeside compound, she lets out a zinger for the ages: “Ah, there’s nothing quite as boring as good old country boredom!” I couldn’t agree more. Given the bucolic setting that Serenbe Playhouse is known for, that’s especially ironic. You may not doze off; but you might find yourself grinding your teeth till this doozy is over.